It is known that secondary alcohols can be oxidized to ketones and cyclic ketones can be oxidized to lactones, hydroxy acids and their derivatives. For example, secondary alcohols can be oxidized by peracids in the presence of strong acids or nitroxides as catalysts. Peracids also oxidize cyclic ketones to lactones or to hydroxy acids in the Baeyer-Villiger reaction. Peracids, persulfuric, perbenzoic, perphthalic, peracetic, and trifluoroperacetic acids may be employed. In some instances peracids can be substituted by concentrated (90%) H.sub.2 O.sub.2 and carboxylic acid anhydride. In all the above processes the main disadvantage is the fact that H.sub.2 O.sub.2 alone will not react and that the necessity to use either peracid or a mixture of an excess of acid anhydride with concentrated (90%) H.sub.2 O.sub.2 cannot be avoided. Peracids are relatively expensive since they have to be prepared either by oxidation of aldehydes, or by a reaction of acid anhydrides with concentrated (90%) H.sub.2 O.sub.2, or from H.sub.2 O.sub.2 and carboxylic acid according to a tedious process where H.sub.2 O is removed by azeotropic distillation. Also, separation of carboxylic acid formed from peracid and the oxidation products may present difficulties. Similarly, peracids have been used to oxidize olefinic double bonds to an epoxide. Allan et al. in U.S. Pat. No. 3,156,709 of Nov. 10, 1964 disclose the oxidation of an olefinic compound with hydrogen peroxide in the presence of catalysts which are inorganic compounds of metals such as osmium, tungsten, vanadium, molybdenum, uranium, niobium, chromium, tantalum, selenium, cerium, ruthenium, titanium, zirconium and thorium forming an insoluble organic compound.
Mimoun in German Pat. No. 1,815,998 issued Dec. 4, 1969 discloses organic peroxide compounds of molybdenum and tungsten, their preparation and their use in the epoxidation of olefinic double bonds by hydrogen peroxide. The organic compounds of molybdenum and tungsten disclosed are peroxide complexes with a carboxylic acid amide and with amides of mineral acids.
Bocard et al. in the French Pat. No. 2,082,811 disclose additional metal peroxo complexes containing as organic ligands oxides of pyridine and heterocyclic nitrogen compounds bound to molybdenum and tungsten for the epoxidation of olefins with hydrogen peroxide. Ferruccio in Italian Pat. No. 919,509 issued Mar. 15, 1972 discloses the utilization of an 8-hydroxy quinoline molybdenum complex as a catalyst for the oxidation of olefinic double bonds with hydrogen peroxide.
One disadvantage of the prior art in epoxidation with H.sub.2 O.sub.2 is the efficiency in the use of H.sub.2 O.sub.2 for oxidation of olefins to epoxides or diols or diol derivatives. Usually a substantial part of H.sub.2 O.sub.2 is decomposed to H.sub.2 O and O.sub.2.
Peroxy molybdate derivatives of organic bases are disclosed by R. G. Beiles and E. M. Beiles in Russian Journal of Organic Chemistry, Vol. 12, No. 4, page 467 (1967). Beiles et al. describe the preparation of complexes of molybdenum and picolinic acid in a sulfuric acid solution and depending upon the relative amount of the reagents used the resulting complexes have 1,2 and 3-amine molecules per molecule of H.sub.2 MoO.sub.6.
Westlake et al. report in C.R. Acad. Sc. Paris, Vol. 280, Series C, page 113 (1975) the preparation of dipicolinic acid complexes of peroxo molybdates and tungstates in an acid medium adjusted by addition of sulfuric acid.
Kerogat et al. in Journal of Fluorine Chemistry 6, 67-75 (1975) further react the dipicolinic acid complexes of peroxo molybdates and tungstates with a stoichiometric amount of fluoride in acetonitrile.